不飽和イソシアナートを用いた新規キラルポリメタクリレートの合成と不斉認識能

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  • Syntheses of Novel Chiral Polymethacrylates Using Unsaturated Isocyanate and Chiral Recognition Ability
  • フホウワ イソシアナート オ モチイタ シンキ キラル ポリメタクリレート ノ ゴウセイ ト フセイ ニンシキノウ

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Chiral methacrylates (RMOC, RMOU) having an urethane or urea bond were synthesized from the reaction of 2-methacryloyloxyethyl isocyanate (MOI) and optically active alcohols or amines, such as cholesterol, L-menthol, amino acid derivatives, cinchonine, (S) methylbenzylamine, (R) -1- (1-naphthyl) ethylamine, and so on. Radical polymerizations of RMOC and RMOU were carried out using azobisisobutyronitrile (AIBN) to obtain corresponding optically active polymers having hydrogen bonds caused by urethane or urea segments. Chiroptical properties of poly (RMOC) and poly (RMOU) were affected by temperature. This may be attributed to change of conformation caused by hydrogen bonds and/or interaction between substituents in the side chain. From the results of radical copolymerizations of RMOC or RMOU with styrene (ST), methyl methacrylate (MMA), or butyl methacrylate (BMA), monomer reactivity ratios (r1, r2) and Alfrey-Price Q-e were determined. Chiroptical properties of the copolymers were strongly influenced by comonomer units. To examine chiral recognition abilities of poly (RMOC) and poly (RMOU), chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were prepared from silica gel, poly (RMOC), and poly (RMOU). The CSPs resolved racemates 1 to 16, and the chiral recognition abilities of poly (RMOC) and poly (RMOU) may be ascribed to the secondary and/or higher-ordered structure of the polymers.

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  • 高分子論文集

    高分子論文集 61 (4), 216-226, 2004

    公益社団法人 高分子学会

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